Disodium 2,3-dihydroxybutanedioate → HCID 86698315, compound

HRID 1050281Notes

Reaction equation

HRID 1050281 reaction equation
[N:1]([C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[CH2:5]1)[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3)=[N+]=[N-].[H-].[Al+3].[Li+].[H-].[H-].[H-].CCOCC.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[Na+]>C1COCC1>[NH2:1][C@H:4]1[CH2:9][C@H:8]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:6]2([CH3:7])[CH2:5]1)[C:18]1[CH:17]=[CH:16][C:15]([O:22][CH3:23])=[CH:14][C:13]=1[CH2:12][CH2:11]3

Participants

6

Reactant 4

HCID 13355Disodium 2,3-dihydroxybutanedioateHCID 21226445Aluminium lithium hydrideHCID 21584184Diethylether waterHCID 86698314HCID 86698314, compound

Product 1

HCID 86698315HCID 86698315, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 1.28 g (4.1 mmol) 16β-azido-3-methoxy-estra-1,3,5(10)-triene in 30 ml abs. THF, 10 ml of a 1M lithium aluminum hydride solution in THF (Fluka) is added dropwise under cooling. The mixture is stirred for further 30 min at RT, followed by cautious addition of ether/water at 0° C. and subsequent addition of sodium tartrate solution. After three subsequent extractions of the aqueous phase with ether, the combined organic phases are washed twice with water, dried with sodium sulfate and concentrated. Yield after recrystallization from hexane: 1.05 g (89%), white solid matter with F=90-94° C.

Workup

  1. temperatureunder cooling
  2. extractionAfter three subsequent extractions of the aqueous phase with ether
  3. washthe combined organic phases are washed twice with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated
  6. customYield
  7. customafter recrystallization from hexane
  8. customwith F=90-94° C.

Sources & evidence

ORD record
ord-dba318140d62484a97d94b8b5b60f423
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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